Medium sized (C.sub.10 -C.sub.16) ring carbocyclic alkyl ethers have found utility in perfume and fragrance formulations (Stroll, M.; Rouve, A. Synthesis of Macrocyclic Products of a Musk Odor. Cyclic Acyloins. Helv. Chim. Acta. 1947, 30, 1822; Haarmann; Reimer Neth. Patent 6,411,715, 1965. Chem. Abstr. 63:8228d (1965)). Their potential in textiles, coatings, and paper applications as odor enhancing materials and non-ionic surfactants are also encouraging (Tong, S. T. Macrocyclic Compounds from Pine Needle Wax. Soap Perfum. Consmet. 1954, 27, 58 Chem. Abstr. 49:2339a (1954)). In the past, these ethers have been prepared by reacting sulfate esters with alkoxide ions, (Williamson, A. W.; J. Chem. Soc. 1852, 4 229), by the alkyloxymercuration of alkenes (March, J. Advanced Organic Chemistry Reactions, Mechanisms, and Structure, 2nd. Ed.; McGraw-Hill: New York, 1978, pp. 357-361), by the reaction of diazoalkanes with carbinols (Neeman, M.; Caserio, C. M.; Roberts, J. D.; Johnson, W. S. Tetrahedron Lett. 1959, 6,36. Chem. Abstr. 53: 17877a (1958)), by the reaction of copper (I) alkoxides with alkyl halides (Whitesides, G. M.; Sadowski, J. S.; Lilburn, J. J. Am. Chem. Soc. 1974, 96, 2829. Chem. Abstr. 81:13039 (1973)), by the reduction of esters with trichlorosilane (Baldwin, S. W.; Haunt, S. A. J. Org Chem. 1975, 40, 3885. Chem. Abstr. 84: 16797k (1975)), or enol ethers with metal catalysts (Verzele, M.; Acke, M.; Anteunis, M. J. Chem. Soc. 1963, 5598). A more general reaction includes an alkyl halide displacement of an alkoxide ion. All of these previous preparations require tedious column chromatographic techniques to obtain uncontaminated product and these preparative difficulties are evidenced by the small number of medium sized (C.sub.10 -C.sub.16) ring syntheses found in the chemical literature.
It was our aim to develop an efficient and economical method to prepare medium sized (C.sub.10 -C.sub.16) ring carbocyclic (C.sub.3 -C.sub.6) alkyl ethers which utilized a minimum number of steps, contained no unwanted byproducts, and required a minimal work-up effort. Until now, all reported syntheses gave low yields of a product that was contaminated with starting alcohol, and was extremely difficult to separate and therefore not an attractive syntheses for commercial use.